Cosmetic Compositions Comprising Esters Based on 2-Propylheptanol

ABSTRACT

The invention relates to the use of esters of 2-propylheptanol with benzoic acid and/or benzoic acid derivatives in cosmetic and/or pharmaceutical preparations. The compounds are distinguished by their particularly light sensory impression.

FIELD OF THE INVENTION

This invention relates to the use of esters of 2-propylheptanol withbenzoic acid and/or benzoic acid derivatives in cosmetic and/orpharmaceutical preparations, to specific esters and to a process fortheir production.

PRIOR ART

Cosmetic hair and skin-care emulsions are expected by the consumer tosatisfy a number of requirements. Apart from the cleansing and caringeffects which determine the particular application, importance isattributed to such diverse parameters as highest possible dermatologicalcompatibility, good lipid-layer-enhancing properties, elegantappearance, optimal sensory impression and shelf life.

Besides a number of surfactants, cosmetic hair- and skin-carepreparations generally contain, above all, oil components and water. Theoil components (emollients) used include, for example, hydrocarbons,ester oils and vegetable and animal oils/fats/waxes. In order to satisfystringent market requirements in regard to sensory properties andoptimal dermatological compatibility, new oil components and emulsifiermixtures are being continuously developed and tested. The use of esteroils in cosmetic products has been known for some time. Because of theirimportance, new processes for their production are also beingcontinuously developed. Branched ester oils in particular impart a“lighter” skin feel and are therefore the subject of intensive research.The use of 2-methyl-1,3-propanediol monoesters is described, forexample, in DE 101 60 681; the use of 2-methyl-1,3-propanediol diestersis described in DE 101 60 682. U.S. Pat. No. 2,921,089 describesdi-(2-propylheptyl)-phthalate and its suitability as a plasticizer forPVC. EP 1 415 978 A1 (Oxeno Olefinchemie GmbH) describes mixturescontaining benzoic acid-2-propylheptyl ester and the use of thesemixtures as plasticizers for polymers, PVC or PVC plastisols and alsotheir use in paints and lacquers, adhesives, adhesive components andsealing compounds.

The problem addressed by the present invention was to provide new esteroils preferably liquid at 20° C. for cosmetic applications which wouldhave an improved profile in regard to their sensory properties(lightness, non-greasy skin feel, softness, spreadability, absorption,distribution behavior, oiliness) and which could be incorporated in anumber of cosmetic formulations. The hydrolysis stability of the estersand their capacity for formulation at low pH values would also be ofinterest in this regard. In addition, the esters would lend themselvesto incorporation both in w/o and in o/w formulations and would becompatible in particular with crystalline UV filters, pigments,antiperspirants, salts and silicones. It has surprisingly been foundthat esters of 2-propylheptanol lead to sensorially light products. Someof these esters and their production are known from DE 103 05 562, butfor a totally different application, namely as polymer additives. WO2006/097235 describes esters of 2-propylheptanol with linear or branchedcarboxylic acids. Unfortunately, these esters are problematic in theformulation of preparations containing UV filters. Above all, theunsatisfactory solubility of the UV filters is a limiting factor.

Accordingly, the problem addressd by the present invention was toprovide esters that would be improved in relation to the prior art, moreparticularly esters which could readily be formulated together with UVfilters and, at the same time, would not have any disadvantages relativeto the prior art in regard to sensory impression.

DESCRIPTION OF THE INVENTION

The present invention relates to the use of esters of 2-propylheptanolwith benzoic acid and/or benzoic acid derivatives in cosmetic and/orpharmaceutical preparations.

Surprisingly, esters propyl-branched in the alkyl chain are particularlysuitable for cosmetic formulations, more particularly for formulationsexpected to impart a “light” skin feel. The esters can be incorporatedparticularly well in various formulations. Liquid substance mixtures areobtained and may be used accordingly as oil components or consistencyfactors according to chain length, branching and number of double bonds.According to the invention, a single 2-propylheptyl ester or a mixtureof various esters may be used.

The present invention relates in particular to the use of esters of2-propylheptanol with benzoic acid and/or benzoic acid derivatives incosmetic and/or pharmaceutical preparations for wetting or impregnatingor coating utility and/or hygiene wipes used for cleaning and/or care ofthe body.

A preferred embodiment of the invention is characterized by the use ofesters with a total of 24 or fewer carbon atoms, preferably 22 or fewercarbon atoms.

The invention encompasses both the use of individual esters of2-propylheptanol with benzoic acid and/or benzoic acid derivatives andthe use of mixtures containing at least one of these esters.

According to the invention, esters of 2-propylheptanol with benzoic acidor benzoic acid derivatives . . . Benzoic acid derivatives in thecontext of the invention are any compounds derived from benzoic acid,the —COOH group remaining unchanged (because it has to be available forthe esterification with 2-propylheptanol).

Suitable benzoic acid derivatives are carboxysubstituted benzoic acids.The term “carboxysubstituted” is used synonymously with “carboxylated”and denotes benzoic acids which cary at least one other —COOH group.Suitable carboxysubstituted benzoic acids are mono- ordi-carboxysubstituted benzoic acids.

Monocarboxy-substituted benzoic acids (=benzene dicarboxylic acids) are,for example, 1,2-benzene dicarboxylic acid (phthalic acid), 1,3-benzenedicarboxylic acid (isophthalic acid or m-phthalic acid),1,4-benzenedicarboxylic acid (terephthalic acid).

Dicarboxy-substituted benzoic acids (=benzene tricarboxylic acids) are,for example, 1,2,3-benzene tricarboxylic acid (=hemimellitic acid),1,2,4-benzene tricarboxylic acid (=trimellitic acid), 1,3,5-benzenetricarboxylic acid.

Tricarboxy-substituted benzoic acids (=benzene tetracarboxylic acids)are, for example 1,2,4,5-benzene tetracarboxylic acid (=pyromelliticacid).

The carboxysubstituted benzoic acids may optionally be alkyl- orhydroxyl-substituted.

Suitable benzoic acid derivatives are alkyl-substituted benzoic acids.The term “alkyl-substituted” is used synonymously with “alkylated” anddenotes benzoic acids which carry at least one other group R on thebenzene ring, the substituents R (independently of one another)representing a linear or branched, saturated or unsaturated alkyl groupcontaining 1 to 8 carbon atoms. Suitable substituents R are, forexample, methyl, ethyl, propyl-, isopropyl [=1-methylethyl-], propenyl-,isobutyl [2-methylpropyl], sec.butyl [=1-methylpropyl], tert.butyl[1,1-dimethylethyl], but-2-enyl, but-3-enyl, but-1-enyl, n-pentyl,1-methylbutyl-, 2-methylbutyl-, 3-methylbutyl, 1-ethylpropyl,1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-pentenyl-,2-pentenyl-, 3-pentenyl-, 4-pentenyl, hexyl-, 1-methylpentyl-,2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl-,2-ethylbutyl-, 3-ethylbutyl-,1-hexenyl, 2-hexenyl, 3-hexenyl,4-hexenyl-, 5-hexenyl, heptyl, 1-methylhexyl-, 2-methylhexyl-,3-methylhexyl-, 4-methylhexyl-, 5-methylhexyl, 1-hepentyl, 2-heptenyl,3-heptenyl-, 4-heptenyl-, 5-heptenyl, 6-heptenyl-, n-octyl,2-ethylhexyl-,1,1,3,3-tetramethylbutyl.

Examples of monoalkyl-substituted benzoic acids are methylbenzoic acids,such as 2-methylbenzoic acid (=o=toluylic acid), 3-methylneboic acid(=m-touylic acid), 4-methylbenzoic acid (=p-toluylic acid) orethylbenzoic acids, such as 2-ethylbenzoic acid, 3-ethylbenzoic acid or4-ethylbenzoic acid. Examples of polyalkyl-substituted benzoic acids are2,4-dimethylbenoic acid, 2,3-dimethylbenzoic acid, 2,5-dimethylbenzoicacid, 2,6-dimethylbenzoic acid or 2,4,5-trimethylbenzoic acid. Thepolyalkyl-substituted benzoic acid derivatives of course also includethose in which the alkyl groups R are not identical, for example2-methyl-4-ethylbenzoic acid.

Other suitable benzoic acid derivatives are hydroxysubstituted benzoicacids. The term “hydroxy-substituted” is used synonymously with“hydroxylated” and denotes benzoic acids which carry at least one othergroup —OH on the benzene ring. Examples of monohydroxy-substitutedbenzoic acids are 2-hydroxybenzoic acid (salicylic acid),3-hydroxybenzoic acid, 4-hydroxybenzoic acid. Examples ofpolyhydroxy-substituted benzoic acids are 2,4-dihydroxybenzoic acid and2,5-dihydroxybenzoic acid.

Other suitable benzoic acid derivatives are hydroxy- andalkyl-substituted benzoic acids. Hydroxy- and alkyl-substituted benzoicacids are benzoic acids which carry at least one —OH group on thebenzene ring and at least one alkyl group R (as defined above for thealkyl-substituted benzoic acids). Examples of hydroxy- andalkyl-substituted benzoic acids are 2-methyl-3-hydroxybenzoic acid and2-ethyl-3-hydroxybenzoic acid.

Other suitable benzoic acid derivatives are derivatives obtainable byacylation of hydroxysubstituted benzoic acids such as, for example,acetylsalicylic acid. The acyl group inserted by acylation can have, forexample, the following formula: —C(═O)—R₁, where R₁ is a linear orbranched, saturated or unsaturated alkyl group containing 1 to 8 carbonatoms.

In a preferred embodiment of the invention, compounds selected from thegroup consisting of methyl-substituted benzoic acids,hydroxy-substituted benzoic acids, carboxy-substituted benzoic acids,derivatives obtainable by acylation of hydroxy-substituted benzoic acidsare used as benzoic acid derivatives.

The expression “esters of 2-propylheptanol with benzene dicarboxylicacids” encompasses both diesters of benzene dicarboxylic acid with2-propylheptanol, i.e. for example di-2-propylhepty1-1,4-benzoic aciddiester [di-2-propylheptyl terephthalic acid], and monoesters, such asfor example 2-propylhepty1-1,4-benzoic acid ester, in which only oneacid group of the benzene dicarboxylic acid is esterified and in whichthe second acid group is free. It also encompasses mixed esters in whichone acid group of the benzene dicarboxylic acid is esterified with2-propylheptanol and the second acid group is esterified with anotheralcohol. One embodiment of the invention is characterized by the use ofmixed esters of benzene dicarboxylic acids (more particularlybenzene-1,4-dicarboxylic acids) and 2-propylheptanol and another alcoholselected from the group consisting of 3-methyl-2-propylhexanol,4-methyl-2-propylhexanol and 5-methyl-2-propylhexanol.

In one embodiment of the invention, the mixed esters are obtained byreaction of the corresponding benzene dicarboxylic acid with a mixturesof 2-propylheptanol, 3-methyl-2-propylhexanol, 4-methyl-2-propylhexanoland 5-methyl-2-propylhexanol.

Another embodiment is characterized by the use of mixed esters ofbenzene dicarboxylic acids and 2-propyl heptanol and another alcoholwith the general formula R—OH, where R is a linear or branched,saturated dor unsaturated alkyl group containing 1 to 12 carbon atoms.

Another embodiment is characterized by the use of mixed esters ofbenzene dicarboxylic acids and 2-propyl heptanol and another alcoholwith the general formula R—OH, where R is a saturated, linear orbranched, alkyl group containing 1 to 12 carbon atoms.

Another preferred embodiment is characterized by the use of mixed estersof benzene dicarboxylic acids and 2-propyl heptanol and another alcohol,the other alcohol being selected from the group consisting of methanol,ethanol, propanol, isopropenol, butanol, isobutanol, pentanol, hexanol,isohexanol, octanol, decanol or dodecanol.

The present invention also relates to esters of 2-propylheptanol withbenzoic acid derivatives excludingdi-[2-propylheptyl]-1,2-benzenedicarboxylic acid ester.

In another preferred embodiment of the invention, compounds selectedfrom the group consisting of methyl-substituted benzoic acids,hydroxy-substituted benzoic acid, carboxy-substituted benzoic acids,derivatives obtainable by acylation of hydroxy-substituted benzoic acidsare used as benzoic acid derivatives.

A preferred embodiment of the invention relates to esters selected fromthe group consisting of di-[2-propylheptyl]-1,4-benzene dicarboxylicacid diester, 2-propylhepty1-1,4-benzene dicarboxylic acid ester,2-propylheptyl-2-hydroxybenzoic acid ester,2-propylheptyl-2-methylbenzoic acid ester,2-propylheptyl-3-methylbenzoic acid ester,2-propylheptyl-4-methylbenzoic acid ester,2-propylheptyl-2-acetoxybenzoic acid ester (=2-propylheptyl acetylsalicylic acid ester).

The invention encompasses both individual esters and mixtures of variousesters.

The present invention relates to compositions containing an ester of2-propylheptanol with benzoic acid derivatives and at least one otherester of the same benzoic acid derivative with an alcohol selected fromthe group consisting of 3-methyl-2-propylhexanol, 4-methyl-2-propylhexanol or 5-methyl-2-propyl hexanol.

In a preferred embodiment of the invention, these compositions contain

-   -   80 to 99.99% by weight of the 2-propylheptyl ester,    -   0.01 to 20% by weight of the corresponding methyl-2-propylhexyl        ester.        The compositions are suitable in cosmetic and/or pharmaceutical        preparations.

The invention also relates to a process for the production of the estersaccording to the invention, in which a mixture containing 2-propylheptanol and the corresponding benzoic acid derivative are reacted.

The process according to the invention also encompasses the productionof ester mixtures in which 2-propylheptanol is reacted together with thecorresponding benzoic acid derivative mixture.

The process according to the invention also encompasses the productionof compositions according to claim 5, in which a mixtures of 2-propylheptanol and at least one alcohol selected from the group consisting of3-methyl-2-propylhexanol, 4-methyl-2-propylhexanol or5-methyl-2-propylheptanol and the corresponding benzoic acid derivativeare reacted.

In a preferred embodiment of the invention, the mixture containingalcohol and the corresponding benzoic acid derivative is reacted in thepresence of an esterification catalyst.

In a preferred embodiment, the mixture containing alcohol and thecorresponding benzoic acid is heated, the water formed is continuouslyremoved and the crude product is distilled. The process may be carriedout in the presence of an esterification catalyst, for example an acidor a base. In a preferred embodiment, the process is carried out in theabsence of solvents, preferably with educts which are substantiallywater-free. A preferred embodiment of the process is characterized bythe use of a tin catalyst. Suitable tin catalysts are, for example, tinoxalate (for example Fascat® 2001), tin oxide (SnO, Fascat® 2000) andtin(IV) catalysts, such as dibutyl tin diacetate (Fascat® 4200), dibutyltin oxide (Fascat® 4201) and dibutyl tin laurate (Fascat® 4202) or tinoxide (SnO) which were once marketed by Atofina, but are now marketed byArkema.

The esterification is preferably carried out at temperatures in therange from 100 to 300° C. and, more particularly, at temperatures in therange from 200 to 250° C.

In another embodiment, at least one enzyme is used as the catalyst.Suitable enzymes are any enzymes or enzyme mixtures known to the expertwhich are capable of catalyzing the esterification of alcohol and acid,for example lipases, acyl transferases and esterases. Theenzyme-catalyzed esterification is typically carried out at temperaturesof 20 to 100° C. and preferably at temperatures of 40 to 80° C.

The present invention also relates to a process for the production ofthe esters according to the invention, in which a mixture containing2-propylheptanol and the methyl ester of the corresponding benzoic acidderivative is reacted in the presence of a transesterification catalyst.

The process according to the invention also encompasses the productionof ester mixtures, in which 2-propylheptanol is reacted together withthe corresponding mixtures of the methyl esters of the correspondingbenzoic acid derivatives acids in the presence of an esterificationcatalyst.

The process according to the invention also encompasses the productionof the compositions claimed in claim 5, in which a mixture of2-propylheptanol and at least one alcohol selected from the groupconsisting of 3-methyl-2-propylhexanol, 40methyl-2-propylhexanol or5-methyl-2-propylhexanol and the methyl ester of the correspondingbenzoic acid derivative is reacted in the presence of atransesterification catalyst.

In a preferred embodiment, the mixture containing alcohol and the methylester of the corresponding benzoic acid derivative is heated in thepresence of the esterification catalyst, the water formed iscontinuously removed and the crude product is distilled. In a preferredembodiment, the process is carried out in the absence of solvents,preferably with educts which are substantially water-free.

The esterification is preferably carried out at temperatures of 100 to300° C. and more particularly at temperatures of 200 to 250° C. Thetransesterification catalyst may be selected from any of thetransesterification catalysts known to the expert, sodium methylate ortetra-alkyl titanate preferably being used.

In another embodiment, at least one enzyme is used as the catalyst.Suitable enzymes are any enzymes or enzyme mixtures known to the expertwhich are capable of catalyzing the transesterification of alcohol andacid methyl ester, for example lipases, acyl transferases and esterases.The enzyme-catalyzed esterification is typically carried out attemperatures of 20 to 100° C. and preferably at temperatures of 40 to80° C.

The expressions “esters of X-methyl-2-propylhexanol with benzenedicarboxylic acids” used in the following encompass both diesters of thebenzene dicarboxylic acids with the particular methyl-2-propylhexanol,i.e. for example di-3-methyl-2-propylhexyl-1,4-benzene dicarboxylic aciddiester or di-5-methyl-2-propylhexyl-1,4-benzene dicarboxylic aciddiester, and also monoesters, such as for example3-methyl-2-propylheptyl-1,4-benzene dicarboxylic acid monoester, andmixed esters in which one acid group of the benzene dicarboxylic acid isesterified with the particular methyl-2-propylhexanol and the secondacid group of the benzene dicarboxylic acid is esterified with a secondalcohol. The second alcohol may be selected from3-methyl-2-propylhexanol, 4-methyl-2-propylhexanol and5-methyl-2-propylhexanol, the second alcohol having to be different fromthe first methyl-2-propylhexanol. In another embodiment of the mixedesters, the second alcohol is selected from the group consisting ofmethanol, ethanol, propanol, isopropanol, butanol, isobutanol, pentanol,hexanol, isohexanol, octanol, decanol and dodecanol.

Esters of 3-methyl-2-propylhexanol with benzoic acid and/or benzoic acidDerivatives

The present invention also relates to esters of 3-methyl-2-propylhexanolwith benzoic acid and/or benzoic acid derivatives and to their use incosmetic and/or pharmaceutical preparations.

One embodiment of the invention is 3-methyl-2-propylhexyl benzoic acid.Another embodiment of the invention isdi-[3-methyl-2-propylhexyl]-1,4-benzoic acid diester.

Esters of 4-methyl-2-propylhexanol with benzoic acid and/or benzoic acidDerivatives

The present invention also relates to esters of 4-methyl-2-propylhexanolwith benzoic acid derivatives.

The present invention also relates to the use of esters of4-methyl-2-propylhexanol with benzoic acid and/or benzoic acidderivatives in cosmetic and/or pharmaceutical preparations.

One embodiment of the invention isdi-[4-methyl-2-propylhexyl]-1,4-benzoic acid diester.

Esters of 5-methyl-2-propylhexanol with benzoic acid and/or benzoic acidDerivatives

The present invention also relates to esters of 4-methyl-2-propylhexanolwith benzoic acid derivatives.

The present invention also relates to the use of esters of5-methyl-2-propylhexanol with benzoic acid and/or benzoic acidderivatives in cosmetic and/or pharmaceutical preparations.

One embodiment of the invention isdi-[5-methyl-2-propylhexyl]-1,4-benzoic acid diester.

The present invention also relates to a process for the production ofesters of 3-methyl-2-propylhexanol with benzoic acid and/or benzoic acidderivatives, in which a mixture containing 3-methyl-2-propylhexanol andthe corresponding acid (carboxylic acid and/or dicarboxylic acid) isreacted. The process according to the invention also encompasses theproduction of ester mixtures, in which 3-methyl-2-propylhexanol isreacted together with the corresponding acid mixtures. The processaccording to the invention also encompasses the production of mixedesters, in which 3-methyl-2-propylhexanol and another alcohol arereacted together with the corresponding dicarboxylic acid.

The present invention also relates to a process for the production ofesters of 4-methyl-2-propylhexanol with benzoic acid derivatives, inwhich a mixture containing 4-methyl-2-propylhexanol and thecorresponding acid (carboxylic acid and/or dicarboxylic acid) isreacted. The process according to the invention also encompasses theproduction of ester mixtures, in which 4-methyl-2-propylhexanol isreacted together with the corresponding acid mixtures. The processaccording to the invention also encompasses the production of mixedesters, in which 4-methyl-2-propylhexanol and another alcohol arereacted together with the corresponding dicarboxylic acid.

The present invention also relates to a process for the production ofesters of 5-methyl-2-propylhexanol with benzoic acid derivatives, inwhich a mixture containing 5-methyl-2-propylhexanol and thecorresponding acid (carboxylic acid and/or dicarboxylic acid) isreacted. The process according to the invention also encompasses theproduction of ester mixtures, in which 5-methyl-2-propylhexanol isreacted together with the corresponding acid mixtures. The processaccording to the invention also encompasses the production of mixedesters, in which 5-methyl-2-propylhexanol and another alcohol arereacted together with the corresponding dicarboxylic acid.

In a preferred embodiment of the invention, the mixture containingalcohol (5-methyl-2-propylhexanol, 4-methyl-2-propylhexanol and/or3-methyl-2-propylhexanol or the other alcohol, if any) and thecorresponding acid is reacted in the presence of an esterificationcatalyst.

In a preferred embodiment of the invention, the mixture containingalcohol (5-methyl-2-propylhexanol, 4-methyl-2-propylhexanol and/or3-methyl-2-propylhexanol or the other alcohol, if any) and thecorresponding acid is heated, the water formed is continuously removedand the crude product is then distilled. The process may be carried outin the presence of an esterification catalyst, for example an acid or abase. In a preferred embodiment, the process is carried out in theabsence of solvents, preferably with educts which are substantiallywater-free. A preferred embodiment of the process is characterized bythe use of a tin catalyst. Suitable tin catalysts are, for example, tinoxalate (for example Fascat® 2001), tin oxide (SnO, Fascat® 2000) andtin(IV) catalysts, such as dibutyl tin diacetate (Fascat® 4200), dibutyltin oxide (Fascat® 4201) and dibutyl tin laurate (Fascat® 4202) or tinoxide (SnO) which were once marketed by Atofina, but are now marketed byArkema.

The esterification is preferably carried out at temperatures in therange from 100 to 300° C. and, more particularly, at temperatures in therange from 200 to 250° C.

In another embodiment, at least one enzyme is used as the catalyst.Suitable enzymes are any enzymes or enzyme mixtures known to the expertwhich are capable of catalyzing the esterification of alcohol and acid,for example lipases, acyl transferases and esterases. Theenzyme-catalyzed esterification is typically carried out at temperaturesof 20 to 100° C. and preferably at temperatures of 40 to 80° C.

The present invention also relates to a process for the production ofesters of 3-methyl-2-propylhexanol with benzoic acid and/or benzoic acidderivatives, in which a mixture containing 3-methyl-2-propylhexanol andthe methyl ester of the corresponding acid is reacted in the presence ofa transesterification catalyst. The process according to the inventionalso encompasses the production of mixed esters, in which3-methyl-2-propylhexanol and another alcohol are reacted together withthe methyl or dimethyl ester of the corresponding dicarboxylic acid inthe presence of a transesterification catalyst.

The present invention also relates to a process for the production ofesters of 4-methyl-2-propylhexanol with benzoic acid derivatives, inwhich a mixture containing 4-methyl-2-propylhexanol and the methyl esterof the corresponding acid is reacted in the presence of atransesterification catalyst. The process according to the inventionalso encompasses the production of mixed esters, in which4-methyl-2-propylhexanol and another alcohol are reacted together withthe methyl or dimethyl ester of the corresponding dicarboxylic acid inthe presence of a transesterification catalyst.

The present invention also relates to a process for the production ofesters of 5-methyl-2-propylhexanol with benzoic acid derivatives, inwhich a mixture containing 5-methyl-2-propylhexanol and the methyl esterof the corresponding acid is reacted in the presence of atransesterification catalyst. The process according to the inventionalso encompasses the production of mixed esters, in which5-methyl-2-propylhexanol and another alcohol are reacted together withthe methyl or dimethyl ester of the corresponding dicarboxylic acid inthe presence of a transesterification catalyst. The process according tothe invention also encompasses the production of ester mixtures, inwhich the alcohol (5-methyl-2-propylhexanol, 4-methyl-2-propylhexanol,3-methyl-2-propylhexanol) is reacted together with the correspondingmixtures of the methyl esters of the acids in the presence of atransesterification catalyst.

In a preferred embodiment, the mixture containing alcohol(5-methyl-2-propylhexanol, 4-methyl-2-propylhexanol,3-methyl-2-propylhexanol) and the methyl ester of the corresponding acidis heated in the presence of the esterification catalyst, the waterformed is continuously removed and the crude product is distilled. In apreferred embodiment, the process is carried out in the absence ofsolvents, preferably with educts which are substantially water-free.

The esterification is preferably carried out at temperatures of 100 to300° C. and more particularly at temperatures of 200 to 250° C. Thetransesterification catalyst used may be selected from any of thoseknown to the expert, sodium methylate or tetra-alkyl titanate beingpreferred.

In another embodiment, at least one enzyme is used as the catalyst.Suitable enzymes are any enzymes or enzyme mixtures known to the expertwhich are capable of catalyzing the transesterification of alcohol andacid methyl ester, for example lipases, acyl transferases and esterases.The enzyme-catalyzed esterification is typically carried out attemperatures of 20 to 100° C. and preferably at temperatures of 40 to80° C.

Cosmetic/Pharmaceutical Preparations

The 2-propylheptyl esters of benzoic acid and/or benzoic acidderivatives allow the production of stable cosmetic and pharmaceuticalemulsions with a particularly light skin feel.

Accordingly, the present invention also relates to cosmetic and/orpharmaceutical preparations containing

-   -   (a) at least one ester of 2-propylheptanol with benzoic acid        and/or benzoic acid derivatives    -   (b) at least one emulsifier and/or surfactant and/or wax        component and/or polymer and/or another oil component.

The preparations according to the invention preferably contain 0.1 to80% by weight, more particularly 0.5 to 70% by weight, preferably 0.75to 60% by weight, more particularly 1 to 50% by weight, preferably 1 to40% by weight of at least one ester of 2-propylheptanol with benzoicacid and/or benzoic acid derivatives.

The present invention also relates to cosmetic and/or pharmaceuticalpreparations containing

-   -   (a) 0.1 to 80% by weight, more particularly 0.1 to 70% by        weight, preferably 0.1 to 60% by weight, more particularly 0.1        to 50% by weight, preferably 0.1 to 40% by weight of at least        one ester of 2-propylheptanol with benzoic acid and/or benzoic        acid derivatives,    -   b) 0.1 to 20% by weight of emulsifier (b-1) and/or surfactant        (b-2) and/or wax component (b-3) and/or polymer (b-4), 0.1 to        40% by weight of other oil components (b-5) and    -   c) 0 to 98% by weight of water.

The preparations according to the invention contain at least 0.1, moreparticularly at least 0.5, more particularly at least 0.75, preferablyat least 1, preferably at least 5% by weight of one or more esters (a).

All percentages by weight represent % by weight, based on the cosmeticand/or pharmaceutical preparation.

In one embodiment of the invention, the preparations contain at leastone ester selected from the group consisting of 2-propylheptyl benzoicacid ester, di[2-propylheptyl]-1,4-benzene dicarboxylic acid diester,2-propylheptyl-1,4-benzene dicarboxylic acid ester,2-propylheptyl-2-hydroxybenzoic acid ester,2-propylheptyl-2-methylbenzoic acid ester,2-propylheptyl-3-methylbenzoic acid ester,2-propylheptyl-4-methylbenzoic acid ester,2-propylheptyl-2-acetoxybenzoic acid ester (=2-propylheptyl acetylsalicylic acid ester).

Another preferred embodiment of the cosmetic and/or pharmaceuticalpreparations contains (a) 0.1 to 80, more particularly 0.1 to 70,preferably 0.1 to 60, preferably 0.1 to 50% by weight of at least oneester of 2-propylheptanol with benzoic acid and/or benzoic acidderivatives, (b) 0.1 to 20% by weight of emulsifiers (b-1) and/orsurfactants (b-2) and/or wax components (b-3) and/or polymers (b-4) and0.1 to 40% by weight of other oil components (b-5) and (c) 0 to 98% byweight of water.

The present invention also relates to cosmetic and/or pharmaceuticalpreparations containing

-   -   (a) at least one ester of 3-methyl-2-propylhexanol with benzoic        acid and/or benzoic acid derivatives    -   (b) at least one emulsifier and/or surfactant and/or wax        component and/or polymer and/or another oil component.

The present invention also relates to cosmetic and/or pharmaceuticalpreparations containing

-   -   (a) at least one ester of 4-methyl-2-propylhexanol with benzoic        acid and/or benzoic acid derivatives    -   (b) at least one emulsifier and/or surfactant and/or wax        component and/or polymer and/or another oil component.

The present invention also relates to cosmetic and/or pharmaceuticalpreparations containing

-   -   (a) at least one ester of 5-methyl-2-propylhexanol with benzoic        acid and/or benzoic acid derivatives    -   (b) at least one emulsifier and/or surfactant and/or wax        component and/or polymer and/or another oil component.

The preparations according to the invention, the compositions accordingto the invention and the esters according to the invention are suitablefor incorporation as a base in all cosmetic body care and cleansingpreparations such as, for example, body oil, baby oil, body milk,creams, lotions, sprayable emulsions, sunscreens, antiperspirants,liquid and bar soaps, etc. They may also be used insurfactant-containing formulations such as, for example, foam and showerbaths, hair shampoos and hair care rinses. They may be applied as a carecomponent to tissues, papers, wipes, nonwovens, sponges, puffs, plastersand bandages which are used in the field of hygiene and care (wet wipesfor baby hygiene and baby care, cleaning wipes, facial wipes, skin carewipes, care wipes containing active ingredients against ageing of theskin, wipes containing sun protection formulations and insect repellentsand wipes for decorative cosmetics or for after-sun treatment, toiletwipes, antiperspirant wipes, diapers, handkerchiefs, wet wipes, hygieneproducts, self-tanning wipes). They may also be used linter alia inhair-care, hair-cleaning or hair-coloring preparations.

Depending on the application envisaged, the cosmetic formulationscontain a number of other auxiliaries and additives such as, forexample, surfactants, other oil components, emulsifiers, pearlizingwaxes, consistency factors, thickeners, superfatting agents,stabilizers, polymers, fats, waxes, lecithins, phospholipids, biogenicagents, UV protection factors, antioxidants, deodorants,antiperspirants, antidandruff agents, film formers, swelling agents,insect repellents, self-tanning agents, tyrosinase inhibitors(depigmenting agents), hydrotropes, solubilizers, preservatives, perfumeoils, dyes, etc. which are listed by way of example in the following.

Emulsifier b-1

In one embodiment of the invention, the preparations according to theinvention contain at least one emulsifier. The compositions according tothe invention contain(s) the emulsifier(s) in a quantity of 0 to 40% byweight, preferably 0.1 to 20% by weight, preferably 0.1 to 15% by weightand more particularly 0.1 to 10% by weight, based on the total weight ofthe composition.

In one embodiment of the invention, the preparation according to theinvention contains more than one emulsifier. Depending on the othercomponents, the expert uses typical emulsifier systems (such as, forexample, emulsifier and co-emulsifier).

Nonionic Emulsifiers

The group of nonionic emulsifiers includes, for example,

-   -   (1) products of the addition of 2 to 50 mol ethylene oxide        and/or 1 to 20 mol propylene oxide onto linear fatty alcohols        containing 8 to 40 carbon atoms, onto fatty acids containing 12        to 40 carbon atoms and onto alkylphenols containing 8 to 15        carbon atoms in the alkyl group;    -   (2) C₁₂₋₁₈ fatty acid monoesters and diesters of products of the        addition of 1 to 50 mol ethylene oxide onto glycerol;    -   (3) sorbitan monoesters and diesters of saturated and        unsaturated fatty acids containing 6 to 22 carbon atoms and        ethylene oxide adducts thereof;    -   (4) alkyl mono- and oligoglycosides containing 8 to 22 carbon        atoms in the alkyl group and ethoxylated analogs thereof;    -   (5) products of the addition of 7 to 60 mol ethylene oxide onto        castor oil and/or hydrogenated castor oil;    -   (6) polyol esters and, in particular, polyglycerol esters such        as, for example, polyolpoly-12-hydroxystearate, polyglycerol        polyricinoleate, polyglycerol diisostearate or polyglycerol        dimerate. Mixtures of compounds from several of these classes        are also suitable;    -   (7) products of the addition of 2 to 15 mol ethylene oxide onto        castor oil and/or hydrogenated castor oil;    -   (8) partial esters based on linear, branched, unsaturated or        saturated C₆₋₂₂ fatty acids, ricinoleic acid and        12-hydroxystearic acid and polyglycerol, pentaerythritol,        dipentaerythritol, sugar alcohols (for example sorbitol), alkyl        glucosides (for example methyl glucoside, butyl glucoside,        lauryl glucoside) and polyglucosides (for example cellulose) or        mixed esters, such as glyceryl stearate citrate and glyceryl        stearate lactate for example;    -   (9) polysiloxane/polyalkyl polyether copolymer or corresponding        derivatives;    -   (10) mixed esters of pentaerythritol, fatty acids, citric acid        and fatty alcohol and/or mixed esters of fatty acids containing        6 to 22 carbon atoms, methyl glucose and polyols, preferably        glycerol or polyglycerol.

The addition products of ethylene oxide and/or propylene oxide ontofatty alcohols, fatty acids, alkylphenols, glycerol monoesters anddiesters and sorbitan monoesters and diesters of fatty acids or ontocastor oil are known commercially available products. They are homologmixtures of which the average degree of alkoxylation corresponds to theratio between the quantities of ethylene oxide and/or propylene oxideand substrate with which the addition reaction is carried out. Theseemulsifiers are w/o or o/w emulsifiers, depending on the degree ofethoxylation. C_(12/18) fatty acid monoesters and diesters of additionproducts of ethylene oxide onto glycerol are known as lipid layerenhancers for cosmetic preparations.

According to the invention, particularly suitable and mild emulsifiersare the polyol poly-12-hydroxystearates and mixtures thereof marketed byCognis Deutschland GmbH under the name of “Dehymuls® PGPH” (w/oemulsifier) or “Eumulgin® VL 75” (mixture with Coco Glucosides in aratio by weight of 1:1, o/w emulsifier) or “Dehymuls® SBL” (w/oemulsifier). Particular reference is made in this connection to EP 0 766661 B1. The polyol component of these emulsifiers may be derived fromsubstances which contain at least two, preferably 3 to 12 and moreparticularly 3 to 8 hydroxyl groups and 2 to 12 carbon atoms.

In principle, suitable lipophilic w/o emulsifiers are emulsifiers withan HLB value of 1 to 8 which are listed in numerous Tables and arewell-known to the expert. Some of these emulsifiers are listed, forexample, in Kirk-Othmer, “Encyclopedia of Chemical Technology”, 3rdEdition, 1979, Vol. 8, page 913. The HLB value for ethoxylated productsmay also be calculated to the following formula: HLB=(100-L): 5, where Lis the percentage by weight of lipophilic groups, i.e. fatty alkyl orfatty acyl groups, in percent by weight in the ethylene oxide adducts.

Of particular advantage from the group of w/o emulsifiers are partialesters of polyols, more particularly C₄₋₆ polyols, such as for examplepartial esters of pentaerythritol or sugar esters, for example sucrosedistearate, sorbitan monoisostearate, sorbitan sesquiisostearate,sorbitan diisostearate, sorbitan triisostearate, sorbitan monooleate,sorbitan sesquioleate, sorbitan dioleate, sorbitan trioleate, sorbitanmonoerucate, sorbitan sesquierucate, sorbitan dierucate, sorbitantrierucate, sorbitan monoricinoleate, sorbitan sesquiricinoleate,sorbitan diricinoleate, sorbitan triricinoleate, sorbitanmonohydroxystearate, sorbitan sesquihydroxystearate, sorbitan dihydroxystearate, sorbitan tri hydroxystearate, sorbitan monotartrate,sorbitan sesquitartrate, sorbitan ditartrate, sorbitan tritartrate,sorbitan monocitrate, sorbitan sesquicitrate, sorbitan dicitrate,sorbitan tricitrate, sorbitan monomaleate, sorbitan sesquimaleate,sorbitan dimaleate, sorbitan trimaleate and technical mixtures thereof.Addition products of 1 to 30 and preferably 5 to 10 mol ethylene oxideonto the sorbitan esters mentioned are also suitable emulsifiers.

Depending on the formulation, it can also be of advantage additionallyto use at least one emulsifier from the group of nonionic o/wemulsifiers (HLB value: 8-18) and/or solubilizers. Examples of suchemulsifiers are the ethylene oxide adducts mentioned at the beginningwith a correspondingly high degree of ethoxylation, for example 10-20ethylene oxide units for o/w emulsifiers and 20-40 ethylene oxide unitsfor so-called solubilizers. Particularly advantageous o/w emulsifiersfor the purposes of the invention are Ceteareth-12 and PEG-20 Stearate.Particularly suitable solubilizers are Eumulgin® HRE 40 (INCI name:PEG-40 Hydrogenated Castor oil), Eumulgin® HRE 60 (INCI name: PEG-60Hydrogenated Castor Oil), Eumulgin® L (INCI name: PPG-1-PEG-9Laurylglycolether) and Eumulgin® SML 20 (INCI name: Polysorbat-20).

Nonionic emulsifiers from the group of alkyl oligoglycosides areparticularly compatible with the skin. C₈₋₂₂ alkyl mono- andoligoglycosides, their production and their use are known from the priorart. They are produced in particular by reacting glucose oroligosaccharides with primary alcohols containing 8 to 22 carbon atoms.So far as the glycoside component is concerned, both monoglycosideswhere a cyclic sugar unit is attached to the fatty alcohol by aglycoside bond and oligomeric glycosides with a degree ofoligomerization of preferably up to about 8 are suitable. The degree ofoligomerization is a statistical mean value on which a homologdistribution typical of such technical products is based. Productsavailable under the name of Plantacare® contain a C₈₋₁₆ alkyl groupattached by a glucosidic bond to an oligoglucoside unit with an averagedegree of oligomerization of 1 to 2. The acyl glucamides derived fromglucamine are also suitable nonionic emulsifiers. The product marketedunder the name of Emulgade® PL 68/50 by Cognis Deutschland GmbH, whichis a 1:1 mixture of alkyl polyglucosides and fatty alcohols, ispreferred for the purposes of the invention. According to the invention,the mixture of Lauryl Glucoside, Polyglyceryl-2-Dipolyhydroxystearate,glycerol and water which is marketed as Eumulgin® VL 75 may also be usedwith advantage in accordance with the invention.

Other suitable emulsifiers are such substances as lecithins andphospholipids. Examples of natural lecithins are the kephalins which arealso known as phosphatidic acids and which are derivatives of1,2-diacyl-sn-glycerol-3-phosphoric acids. By contrast, phospholipidsare generally understood to be mono- and preferably diesters ofphosphoric acid with glycerol (glycerophosphates) which are generallyclassed as fats. Sphingosines and sphingolipids are also suitable asfat-like substances.

Surfactants b-2)

In one embodiment of the invention, the preparations according to theinvention contain at least one surfactant. The surfactant(s) may beselected from anionic, nonionic, cationic and/or amphoteric orzwitterionic surfactants. Surfactant-containing cosmetic preparations,such as for example shower gels, foam baths, shampoos, etc., preferablycontain at least one anionic surfactant.

The compositions according to the invention contain the surfactant(s) ina quantity of 0 to 40% by weight, preferably 0 to 20% by weight,preferably 0.1 to 15% by weight and more particularly 0.1 to 10% byweight, based on the total weight of the composition.

Typical examples of nonionic surfactants are fatty alcohol polyglycolethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters,fatty acid amide polyglycol ethers, fatty amine polyglycol ethers,alkoxylated triglycerides, mixed ethers and mixed formals, optionallypartly oxidized alk(en)yl oligoglycosides or glucuronic acidderivatives, fatty acid-N-alkyl glucamides, protein hydrolyzates(particularly wheat-based vegetable products), polyol fatty acid esters,sugar esters, sorbitan esters, polysorbates and amine oxides. If thenonionic surfactants contain polyglycol ether chains, they may have aconventional homolog distribution, although they preferably have anarrow-range homolog distribution.

Zwitterionic surfactants are surface-active compounds which contain atleast one quaternary ammonium group and at least one —COO⁽⁻⁾ or —SO₃ ⁽⁻⁾group in the molecule. Particularly suitable zwitterionic surfactantsare the so-called betaines, such as the N-alkyl-N,N-dimethyl ammoniumglycinates, for example cocoalkyl dimethyl ammonium glycinate,N-acylaminopropyl-N,N-dimethyl ammonium glycinates, for examplecocoacylaminopropyl dimethyl ammonium glycinate, and2-alkyl-3-carboxymethyl-3-hydroxyethyl imidazolines containing 8 to 18carbon atoms in the alkyl or acyl group and cocoacylaminoethylhydroxyethyl carboxymethyl glycinate. The fatty acid amide derivativeknown under the CTFA name of Cocamidopropyl Betaine is particularlypreferred.

Ampholytic surfactants are also suitable, particularly asco-surfactants. Ampholytic surfactants are surface-active compoundswhich, in addition to a C₈₋₁₈ alkyl or acyl group, contain at least onefree amino group and at least one —COOH— or —SO₃H— group in the moleculeand which are capable of forming inner salts. Examples of suitableampholytic surfactants are N-alkyl glycines, N-alkyl propionic acids,N-alkylaminobutyric acids, N-alkyliminodipropionic acids,N-hydroxyethyl-N-alkylamidopropyl glycines, N-alkyl taurines, N-alkylsarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acidscontaining around 8 to 18 carbon atoms in the alkyl group. Particularlypreferred ampholytic surfactants are N-cocoalkylaminopropionate,cocoacylaminoethyl aminopropionate and C_(12/18) acyl sarcosine.

Anionic surfactants are characterized by a water-solubilizing anionicgroup such as, for example, a carboxylate, sulfate, sulfonate orphosphate group and a lipophilic group. Dermatologically safe anionicsurfactants are known to the expert in large numbers from relevanttextbooks and are commercially available. They are, in particular, alkylsulfates in the form of their alkali metal, ammonium or alkanolammoniumsalts, alkylether sulfates, alkylether carboxylates, acyl isethionates,acyl sarcosinates, acyl taurines containing linear C₁₂₋₁₈ alkyl or acylgroups and sulfosuccinates and acyl glutamates in the form of theiralkali metal or ammonium salts.

Particularly suitable cationic surfactants are quaternary ammoniumcompounds, preferably ammonium halides, more especially chlorides andbromides, such as alkyl trimethyl ammonium chlorides, dialkyl dimethylammonium chlorides and trialkyl methyl ammonium chlorides, for examplecetyl trimethyl ammonium chloride, stearyl trimethyl ammonium chloride,distearyl dimethyl ammonium chloride, lauryl dimethyl ammonium chloride,lauryl dimethyl benzyl ammonium chloride and tricetyl methyl ammoniumchloride. In addition, the readily biodegradable quaternary estercompounds, such as for example the dialkyl ammonium methosulfates andmethyl hydroxyalkyl dialkoyloxyalkyl ammonium methosulfates marketedunder the name of Stepantex® and the corresponding products of theDehyquart® series, may be used as cationic surfactants. “Esterquats” aregenerally understood to be quaternized fatty acid triethanolamine estersalts. They can provide the compositions with particular softness. Theyare known substances which are prepared by the relevant methods oforganic chemistry. Other cationic surfactants suitable for use inaccordance with the invention are the quaternized protein hydrolyzates.

Wax Component b-3)

In one embodiment of the invention, the preparations according to theinvention contain at least one wax component. The compositions accordingto the invention contain the wax component(s) in a quantity of 0 to 40%by weight, more particularly 0 to 20% by weight, preferably 0.1 to 15%by weight and more particularly 0.1 to 10% by weight, based on the totalweight of the composition.

Waxes are normally understood to be natural or synthetic substances andmixtures having the following properties: they have a solid to brittlehard consistency, are coarsely to finely crystalline, transparent toopaque and melt above 30° C. without decomposing. Even slightly abovetheir melting point, they are low in viscosity and non-stringing and arevery temperature-dependent in their consistency and solubility. A singlewax component or a mixture of wax components melting at or above 30° C.may be used in accordance with the invention.

According to the invention, fats and fat-like substances with a wax-likeconsistency may also be used as waxes providing they have the requiredmelting point. These include inter alia fats (triglycerides), mono- anddiglycerides, natural and synthetic waxes, fat and wax alcohols, fattyacids, esters of fatty alcohols and fatty acids and fatty acid amides ormixtures of these substances.

Fats in the context of the invention are understood to betriacylglycerols, i.e. the triple esters of fatty acids with glycerol.The triacylglycerols preferably contain saturated, unbranched andunsubstituted fatty acid components. They may also be mixed esters, i.e.triple esters of glycerol with various fatty acids. So-called hardenedfats and oils obtained by partial hydrogenation may be used inaccordance with the invention and are particularly suitable asconsistency factors. Vegetable hardened fats and oils, for examplehardened castor oil, peanut oil, soybean oil, colza oil, rapeseed oil,cottonseed oil, soybean oil, sunflower oil, palm oil, palm kernel oil,linseed oil, almond oil, corn oil, olive oil, sesame oil, cocoa butterand coconut fat, are preferred.

Suitable fats are inter alia the triple esters of glycerol with C₁₂₋₆₀fatty acids and in particular C₁₂₋₃₆ fatty acids. These includehydrogenated castor oil, a triple ester of glycerol and a hydroxystearicacid which is marketed, for example, under the name of Cutina® HR.Glycerol tristearate, glycerol tribehenate (for example Syncrowax® HRC),glycerol tripalmitate or the triglyceride mixtures known under the nameof Syncrowax® HGLC are also suitable providing the melting point of thewax component or the mixture is 30° C. or higher.

According to the invention, suitable wax components are, in particular,mono- and diglycerides and mixtures of these partial glycerides.Glyceride mixtures suitable for use in accordance with the inventioninclude the products Novata® AB and Novata® B (mixture of C₁₂₋₁₈ mono-,di- and triglycerides) and Cutina® MD or Cutina® GMS (glyceryl stearate)marketed by Cognis Deutschland GmbH & Co. KG.

The fatty alcohols suitable for use as a wax component in accordancewith the invention include C₁₂₋₅₀ fatty alcohols. The fatty alcohols maybe obtained from natural fats, oils and waxes such as, for example,myristyl alcohol, 1-pentadecanol, cetyl alcohol, 1-heptadecanol, stearylalcohol, 1-nonadecanol, arachidyl alcohol, 1-heneicosanol, behenylalcohol, brassidyl alcohol, lignoceryl alcohol, ceryl alcohol or myricylalcohol. According to the invention, saturated unbranched fatty alcoholsare preferred. However, unsaturated, branched or unbranched fattyalcohols may also be used as the wax component in accordance with theinvention providing they have the required melting point. Other suitablefatty alcohols are the fatty alcohol cuts obtained in the reduction ofnaturally occurring fats and oils such as, for example, bovine tallow,peanut oil, colza oil, cottonseed oil, soybean oil, sunflower oil, palmkernel oil, linseed oil, castor oil, corn oil, rapeseed oil, sesame oil,cocoa butter and coconut oil. However, synthetic alcohols, for examplethe linear, even-numbered fatty alcohols from Ziegler's synthesis(Alfols) or the partly branched alcohols from the oxosynthesis(Dobanols) may also be used. C₁₄₋₂₂ fatty alcohols marketed for exampleby Cognis Deutschland GmbH under the name of Lanette® 16 (C₁₆ alcohol),Lanette® 14 (C₁₄ alcohol), Lanette® O (C_(16/18) alcohol) and Lanette®22 (C_(18/22) alcohol) are particularly suitable for the purposes of theinvention. Fatty alcohols give the compositions a dryer feeling on theskin than triglycerides.

C₁₄₋₄₀ fatty acids or mixtures thereof may also be used as waxcomponents. These include, for example, myristic, pentadecanoic,palmitic, margaric, stearic, nonadecanoic, arachic, behenic, lignoceric,cerotic, melissic, erucic and elaeostearic acid and substituted fattyacids such as, for example, 12-hydroxystearic acid, and the amides ormonoethanolamides of the fatty acids. This list is meant to be purelyexemplary without any limiting character.

Waxes suitable for use in accordance with the invention are, forexample, natural vegetable waxes, such as candelilla wax, carnauba wax,Japan wax, espartograss wax, cork wax, guaruma wax, rice oil wax, sugarcane wax, ouricury wax, montan wax, sunflower wax, fruit waxes, such asorange waxes, lemon waxes, grapefruit wax, bayberry wax, and animalwaxes such as, for example, beeswax, shellac wax, spermaceti, wool waxand uropygial fat. According to the invention, it can be of advantage touse hydrogenated or hardened waxes. Natural waxes usable in accordancewith the invention also include the mineral waxes, such as ceresine andozocerite for example, or the petrochemical waxes, for examplepetrolatum, paraffin waxes and microwaxes. Other suitable wax componentsare chemically modified waxes, more particularly the hard waxes such as,for example, montan ester waxes, sasol waxes and hydrogenated jojobawaxes. Synthetic waxes usable in accordance with the invention include,for example, wax-like polyalkylene waxes and polyethylene glycol waxes.Vegetable waxes are preferred for the purposes of the invention.

The wax component may also be selected from the group of wax esters ofsaturated and/or unsaturated, branched and/or unbranchedalkanecarboxylic acids and saturated and/or unsaturated, branched and/orunbranched alcohols, from the group of esters of aromatic carboxylicacids, dicarboxylic acids, tricarboxylic acids and hydroxycarboxylicacids (for example 12-hydroxystearic acid) and saturated and/orunsaturated, branched and/or unbranched alcohols and also from the groupof lactides of long-chain hydroxycarboxylic acids. Examples of esterssuch as these include, for example, C₁₆₋₄₀ alkyl stearates, C₂₀₋₄₀ alkylstearates (for example Kesterwachs® K82H), C₂₀₋₄₀ dialkyl esters ofdimer acids, C₁₈₋₃₈ alkyl hydroxystearoyl stearates or C₂₀₋₄₀ alkylerucates. Other suitable wax components which may be used are C₃₀₋₅₀alkyl beeswax, tristearyl citrate, triisostearyl citrate, stearylheptanoate, stearyl octanoate, trilauryl citrate, ethylene glycoldipalmitate, ethylene glycol distearate, ethylene glycoldi(12-hydroxystearate), stearyl stearate, palmityl stearate, stearylbehenate, cetyl ester, cetearyl behenate and behenyl behenate.

Polymers b-4)

In one embodiment of the invention, the preparations according to theinvention contain at least one polymer. The compositions according tothe invention contain the polymer(s) in a quantity of 0 to 20% byweight, preferably 0.1 to 15% by weight and, more particularly, 0.1 to10% by weight, based on the total weight of the composition.

Suitable cationic polymers are, for example, cationic cellulosederivatives such as, for example, the quaternized hydroxyethyl celluloseobtainable from Amerchol under the name of Polymer JR 400®, cationicstarch, copolymers of diallyl ammonium salts and acrylamides,quaternized vinyl pyrrolidone/vinyl imidazole polymers such as, forexample, Luviquat® (BASF), condensation products of polyglycols andamines, quaternized collagen polypeptides such as, for example,Lauryldimonium Hydroxypropyl Hydrolyzed Collagen (Lamequat® L, Grünau),quaternized wheat polypeptides, polyethyleneimine, cationic siliconepolymers such as, for example, amodimethicone, copolymers of adipic acidand dimethylaminohydroxypropyl diethylenetriamine (Cartaretine®,Sandoz), copolymers of acrylic acid with dimethyl diallyl ammoniumchloride (Merquat® 550, Chemviron), polyaminopolyamides, cationic chitinderivatives such as, for example, quaternized chitosan, optionally inmicrocrystalline distribution, condensation products of dihaloalkyls,for example dibromobutane, with bis-dialkylamines, for examplebis-dimethylamino-1,3-propane, cationic guar gum such as, for example,Jaguar®CBS, Jaguar®C-17, Jaguar®C-16 of Celanese, quaternized ammoniumsalt polymers such as, for example, Mirapol® A-15, Mirapol® AD-1,Mirapol® AZ-1 of Miranol. Suitable anionic, zwitterionic, amphoteric andnonionic polymers are, for example, vinyl acetate/crotonic acidcopolymers, vinyl pyrrolidone/vinyl acrylate copolymers, vinylacetate/butyl maleate/isobornyl acrylate copolymers, methylvinylether/maleic anhydride copolymers and esters thereof, uncrosslinkedand polyol-crosslinked polyacrylic acids, acrylamidopropyltrimethylammonium chloride/acrylate copolymers, octylacrylamide/methylmethacrylate/tert.-butylaminoethyl methacrylate/2-hydroxypropylmethacrylate copolymers, polyvinyl pyrrolidone, vinyl pyrrolidone/vinylacetate copolymers, vinyl pyrrolidone/dimethylaminoethylmethacrylate/vinyl caprolactam terpolymers and optionally derivatizedcellulose ethers and silicones.

Other suitable polymers are polysaccharides, more particularly xanthangum, guar guar, agar agar, alginates and tyloses.

Other Oil Components b-5)

Body-care preparations, such as creams, body oils, lotions and milks,typically contain a number of other oil components and emollients whichcontribute towards further optimizing the sensory properties. The oilcomponents (esters according to the invention plus other oil components)are typically present in a total quantity of 0.1 to 80, moreparticularly 0.5 to 70, preferably 1 to 60, more particularly 1 to 50%by weight, more particularly 1 to 40% by weight, preferably 5 to 25% byweight and more particularly 5 to 15% by weight. The other oilcomponents are typically present in a quantity of 0.1 to 40% by weight.

The other oil components may be selected, for example, from Guerbetalcohols based on fatty alcohols containing 6 to 18 and preferably 8 to10 carbon atoms and other additional esters, such as myristyl myristate,myristyl palmitate, myristyl stearate, myristyl isostearate, myristyloleate, myristyl behenate, myristyl erucate, cetyl myristate, cetylpalmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetylbehenate, cetyl erucate, stearyl myristate, stearyl palmitate, stearylstearate, stearyl isostearate, stearyl oleate, stearyl behenate, stearylerucate, isostearyl myristate, isostearyl palmitate, isostearylstearate, isostearyl isostearate, isostearyl oleate, isostearylbehenate, isostearyl oleate, oleyl myristate, oleyl palmitate, oleylstearate, oleyl isostearate, oleyl oleate, oleyl behenate, oleylerucate, behenyl myristate, behenyl palmitate, behenyl stearate, behenylisostearate, behenyl oleate, behenyl behenate, behenyl erucate, erucylmyristate, erucyl palmitate, erucyl stearate, erucyl isostearate, erucyloleate, erucyl behenate and erucyl erucate. Also suitable are esters ofC₁₈₋₃₈ alkylhydroxycarboxylic acids with linear or branched C₆₋₂₂ fattyalcohols, more especially Dioctyl Malate, esters of linear and/orbranched fatty acids with polyhydric alcohols (for example propyleneglycol, dimer diol or trimer triol), triglycerides based on C₆₋₁₀ fattyacids, liquid mono-, di- and triglyceride mixtures based on C₆₋₁₈ fattyacids, esters of C₆₋₂₂ fatty alcohols and/or Guerbet alcohols witharomatic carboxylic acids, more particularly benzoic acid, esters ofC₂₋₁₂ dicarboxylic acids with polyols containing 2 to 10 carbon atomsand 2 to 6 hydroxyl groups, vegetable oils, branched primary alcohols,substituted cyclohexanes, linear and branched C₆₋₂₂ fatty alcoholcarbonates such as, for example, Dicaprylyl Carbonate (Cetiol® CC),Guerbet carbonates based on fatty alcohols containing 6 to 18 andpreferably 8 to 10 carbon atoms, esters of benzoic acid with linearand/or branched C₆₋₂₂ alcohols (for example Finsolv® TN), linear orbranched, symmetrical or nonsymmetrical dialkyl ethers containing 6 to22 carbon atoms per alkyl group such as, for example, Dicaprylyl Ether(Cetiol® OE), ring opening products of epoxidized fatty acid esters withpolyols and hydrocarbons or mixtures thereof (Cetiol® DD).

Other Ingredients

Suitable thickeners are, for example, Aerosil® types (hydrophilicsilicas), carboxymethyl cellulose and hydroxyethyl and hydroxypropylcellulose, polyvinyl alcohol, polyvinyl pyrrolidone and bentonites, forexample Bentone® Gel VS-5PC (Rheox).

UV protection factors in the context of the invention are, for example,organic substances (light filters) which are liquid or crystalline atroom temperature and which are capable of absorbing ultravioletradiation and of releasing the energy absorbed in the form oflonger-wave radiation, for example heat. UV-B filters can be oil-solubleor water-soluble. Typical UV-A filters are, in particular, derivativesof benzoyl methane. The UV-A and UV-B filters may of course also be usedin the form of mixtures, for example combinations of the derivatives ofbenzoyl methane, for example 4-tert.butyl-4′-methoxydibenzoylmethane(Parsol® 1789) and 2-cyano-3,3-phenylcinnamic acid-2-ethyl hexyl ester(Octocrylene) and esters of cinnamic acid, preferably 4-methoxycinnamicacid-2-ethyl hexyl ester and/or 4-methoxycinnamic acid propyl esterand/or 4-methoxycinnamic acid isoamyl ester. Combinations such as theseare often combined with water-soluble filters such as, for example,2-phenylbenzimidazole-5-sulfonic acid and alkali metal, alkaline earthmetal, ammonium, alkylammonium, alkanolammonium and glucammonium saltsthereof.

Besides the soluble substances mentioned, insoluble light-blockingpigments, i.e. finely dispersed metal oxides or salts, may also be usedfor this purpose. Examples of suitable metal oxides are, in particular,zinc oxide and titanium dioxide. Besides the two groups of primary sunprotection factors mentioned above, secondary sun protection factors ofthe antioxidant type may also be used. Secondary sun protection factorsof the antioxidant type interrupt the photochemical reaction chain whichis initiated when UV rays penetrate into the skin.

In the context of the invention, biogenic agents are, for example,tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid,(deoxy)ribonucleic acid and fragmentation products thereof, β-glucans,retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, aminoacids, ceramides, pseudoceramides, essential oils, plant extracts, forexample prunus extract, bambara nut extract, and vitamin complexes.

Deodorizing components counteract, mask or eliminate body odors. Bodyodors are formed through the action of skin bacteria on apocrineperspiration which results in the formation of unpleasant-smellingdegradation products. Accordingly, suitable deodorizing components areinter alia germ inhibitors, enzyme inhibitors, odor absorbers or odormaskers.

Suitable insect repellents are N,N-diethyl-m-toluamide, pentane-1,2-diolor 3-(N-n-butyl-N-acetylamino)-propionic acid ethyl ester), which ismarketed as Insect Repellent 3535 by Merck KGaA, andButylacetylaminopropionate.

A suitable self-tanning agent is, for example, dihydroxyacetone.Suitable tyrosine inhibitors, which prevent the formation of melanin andare used in depigmenting agents, are, for example, arbutin, ferulicacid, koji acid, coumaric acid and ascorbic acid (vitamin C).

Suitable preservatives are, for example, phenoxyethanol, formaldehydesolution, parabens, pentanediol or sorbic acid and the silver complexesknown under the name of Surfacine® and the other classes of compoundslisted in Appendix 6, Parts A and B of the Kosmetik-verordnung(“Cosmetics Directive”).

Suitable perfume oils are mixtures of natural and synthetic perfumes.Natural perfumes are extracts of flowers, stems and leaves, fruits,fruit peel, roots, woods, herbs and grasses, needles and branches,resins and balsams. Also suitable are animal raw materials, for examplecivet and beaver, and synthetic perfume compounds of the ester, ether,aldehyde, ketone, alcohol and hydrocarbon type.

Suitable pearlizing waxes, particularly for use in surfactant-containingformulations, are, for example, alkylene glycol esters, especiallyethylene glycol distearate; fatty acid alkanolamides, especiallycocofatty acid diethanolamide; partial glycerides, especially stearicacid monoglyceride; esters of polybasic, optionally hydroxysubstitutedcarboxylic acids with fatty alcohols containing 6 to 22 carbon atoms,especially long-chain esters of tartaric acid; fatty compounds, such asfor example fatty alcohols, fatty ketones, fatty aldehydes, fatty ethersand fatty carbonates which contain in all at least 24 carbon atoms,especially laurone and distearylether; fatty acids, such as stearicacid, hydroxystearic acid or behenic acid, ring opening products ofolefin epoxides containing 12 to 22 carbon atoms with fatty alcoholscontaining 12 to 22 carbon atoms and/or polyols containing 2 to 15carbon atoms and 2 to 10 hydroxyl groups and mixtures thereof.

Superfatting agents may be selected from such substances as, forexample, lanolin and lecithin and also polyethoxylated or acylatedlanolin and lecithin derivatives, polyol fatty acid esters,monoglycerides and fatty acid alkanolamides, the fatty acidalkanolamides also serving as foam stabilizers.

Metal salts of fatty acids such as, for example, magnesium, aluminiumand/or zinc stearate or ricinoleate may be used as stabilizers.

In addition, hydrotropes, for example ethanol, isopropyl alcohol orpolyols, may be used to improve flow behavior. Suitable polyolspreferably contain 2 to 15 carbon atoms and at least two hydroxylgroups. The polyols may contain other functional groups, more especiallyamino groups, or may be modified with nitrogen.

The preparations according to the invention, the compositions accordingto the invention and the esters according to the invention are suitable,particularly in cosmetic and/or pharmaceutical preparations, for wettingor impregnating or coating utility and hygiene wipes which are used forcare and/or cleansing of the body.

Examples of utility and hygiene wipes include tissues, papers, wipes,nonwovens, sponges, puffs, plasters and bandages which are used in thefield of hygiene and care. These may be wet wipes for baby hygiene andbaby care, cleaning wipes, facial wipes, skin care wipes, care wipescontaining active ingredients against ageing of the skin, wipescontaining sun protection formulations and insect repellents and wipesfor decorative cosmetics or for after-sun treatment, toilet wipes,antiperspirant wipes, diapers, handkerchiefs, wet wipes, hygieneproducts and self-tanning wipes.

1. A method of preparing cosmetic and/or pharmaceutical preparationscomprising adding to a cosmetic and/or pharmaceutical base, at least oneester of 2-propylheptanol with benzoic acid and/or a benzoic acidderivative.
 2. The method of claim 1 said benzoic acid derivative isselected from the group consisting of methyl-substituted benzoic acids,hydroxy-substituted benzoic acids, carboxy-substituted benzoic acids,and derivatives obtained by acylation of hydroxy-substituted benzoicacids.
 3. An ester of 2-propylheptanol with a benzoic acid derivative,excluding di-[2-propylheptyl]-1,2-benzenedicarboxylic acid ester.
 4. Theester of claim 3 selected from the group consisting ofdi-[2-propylheptyl]-1,4-benzene dicarboxylic acid diester,2-propylheptyl-1,4-benzene dicarboxylic acid ester,2-propylheptyl-2-hydroxybenzoic acid ester,2-propylheptyl-2-methylbenzoic acid ester,2-propylheptyl-3-methylbenzoic acid ester,2-propylheptyl-4-methylbenzoic acid ester, and2-propylheptyl-2-acetoxybenzoic acid ester.
 5. A cosmetic and/orpharmaceutical composition comprising at least one ester of2-propylheptanol with a benzoic acid derivative and at least one otherester of the same benzoic acid derivative with an alcohol selected fromthe group consisting of 3-methyl-2-propylhexanol, 4-methyl-2-propylhexanol and 5-methyl-2-propyl hexanol.
 6. A process for the productionof the ester of claim 3 wherein a mixture containing 2-propylheptanoland the corresponding benzoic acid derivative is reacted.
 7. A processfor the production of the ester of claim 3 wherein a mixture containing2-propylheptanol and the methyl ester of the corresponding benzoic acidderivative is reacted in the presence of a transesterification catalyst.8. A cosmetic and/or pharmaceutical composition comprising: (a) at leastone ester of 2-propylheptanol with benzoic acid and/or a benzoic acidderivative, and (b) at least one emulsifier (b-1), and/or surfactant(b-2), and/or wax component (b-3), and/or polymer (b-4), and/or anotheroil component (b-5).
 9. The composition of claim 8 comprising 0.1 to 80%by weight of at least one ester of 2-propylheptanol with benzoic acidand/or a benzoic acid derivative.
 10. The composition of claim 9comprising: a) 0.1 to 80% by weight of at least one ester of2-propylheptanol with benzoic acid and/or a benzoic acid derivative, b)0.1 to 20% by weight of at least one emulsifier (b-1), and/or surfactant(b-2), and/or wax component (b-3), and/or polymer (b-4); 0.1 to 40% byweight of at least one other oil component (b-5), and (c) 0 to 98% byweight of water.
 11. The composition of claim 8 comprising 0.1 to 40% byweight of at least one ester of 2-propylheptanol with benzoic acidand/or a benzoic acid derivative.
 12. The composition of claim 9comprising: a) 0.1 to 40% by weight of at least one ester of2-propylheptanol with benzoic acid and/or a benzoic acid derivative, b)0.1 to 20% by weight of at least one emulsifier (b-1), and/or surfactant(b-2), and/or wax component (b-3), and/or polymer (b-4); 0.1 to 40% byweight of at least one other oil component (b-5), and (c) 0 to 98% byweight of water.